Key West Vacation Rentals

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Search nearly 100 Key West vacation rentals ranging from intimate 2 bedroom cottages to large 6 bedroom homes. With properties in popular Key West communities like Truman Annex, Key West Golf Club, and 1800 Atlantic plus a variety of pet friendly and monthly rentals, we are sure we have the perfect fit for your trip. Our local Key West team of vacation rental experts has been helping travelers plan amazing vacations for decades and loves to share their local knowledge. Don't hesitate to contact us with questions or for help finding the perfect rental and booking your Key West vacation!

Displaying 37 - 48 of 75 rentals matching your search criteria
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Cottage by the Pool

Type

  • Townhouse
Stock Island
2 Bedrooms
1.5 Baths
4 Guests

In this cozy home you will find yourself nestled in the center of the Key West Golf Club on a secluded lane that cuts through the heart of its community.

Buena Vista

Type

  • Townhouse
Old Town
2 Bedrooms
2.5 Baths
6 Guests

The historic brick foundry residence is in the luxurious gated community of the Truman Annex, appropriately named after President Harry Truman.

Atlantic Paradise

Type

  • Condominium
Ocean Side
2 Bedrooms
2 Baths
6 Guests

Imagine swimming in the Olympic sized pool and enjoying a spectacular view of the Atlantic Ocean at the same time. How about an evening stroll through the tropical jungle in your own backyard.

Paradise Place

Type

  • Condominium
Old Town
1 Bedroom
1 Bath
4 Guests

Cozy apartment within biking distance to The Historic Seaport, Cuban Coffee Queen, local grocery store Fausto's and even Higgs Beach.

Flagler Station

Type

  • House
Mid Town
3 Bedrooms
2 Baths
6 Guests

With family in mind, this lovely 3 bed, 2 bath private home has plenty to offer with a private outdoor pool and patio space. Spend your days enjoying paradise in this spacious monthly rental. This one is a priceless gem!

Conch Adventure

Type

  • Condominium
Old Town
2 Bedrooms
1 Bath
4 Guests

Nestled in a quiet corner of the Shipyard section in the desirable Truman Annex, this 2-bedroom 1 bath downstairs condo offers peace, quiet and convenience.

Papa's Cottage Retreat

Type

  • House
Old Town
1 Bedroom
1 Bath
2 Guests

As you step through the natural wooden gate onto the brick pathway, you will be embraced by this private garden oasis.

Shrimp Party

Type

  • Townhouse
Old Town
2 Bedrooms
2 Baths
4 Guests

Gated compound walking distance to Duval Street but behind the gates quiet solitude in your beautiful home with front porch overlooking the sparking pool.

Tropical Dreaming

Type

  • House
Old Town
2 Bedrooms
2.5 Baths
6 Guests

Do not look any further! Your perfect vacation home rental is right here! Offering a private pool with lounge chairs and covered outside porch. You can also bring your Fido!

Duval Breeze

Type

  • Townhouse
Old Town
2 Bedrooms
2.5 Baths
6 Guests

Location! Location! Location! Duval Breeze offers the best location in town! Walking distance to restaurants, bars and galleries and easy biking distance to the beaches!

Conch Republic Retreat

Type

  • Cottage
Old Town
2 Bedrooms
2 Baths
4 Guests

Located in the quiet neighborhood of The Meadows, you’ll find the Conch Republic Retreat, a quintessential cigar maker’s shotgun style house, circa 1890.

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